Traveling to Oahu? 10 Ways to Make Your Trip More Authentic

by Austin Weihmiller /
Austin Weihmiller's picture
Dec 08, 2016 / 0 comments

Hawaii. Dreamy, warm, beautiful Hawaii. An island paradise nestled in the blue Pacific. It’s pretty nice I must say, but there is way more to the island than Waikiki and Disney’s Aulani. Here’s an insider’s guide to Oahu and its hidden gems.

Traveling to Oahu? 10 ways to make your trip more authentic


Before we get started though, I must lay out the ground rules:

Rule Number One: In Hawaii, there is no such thing as ’flip flops’. If you utter those two silly words, everyone around you will instantly know you’re a tourist. Instead, we use the island vernacular, which translates to slippers. Nope, not those fufu bedtime things you wear, but the shoes you wear out and about. I know, it’s weird! But on visiting Hawaii, you’ll discover Hawaii is a silly, weird place. A good weird though.

Rule Number Two: Learn these phrases: Mauka and Makai. Mauka (mow-kah) means the mountain side of something. Makai (mah-kigh) means the ocean side of something. Kai means water in Hawaiian. Locals will use these two words all the time in giving directions.

swim zone

10. You’ve arrived! Time to hit Waikiki!

Waikiki Beach is a must if it’s your first time visiting the islands. A one-way boulevard runs parallel with the water, and stops at just about every single hotel. The first two hotels were built during World War II—The Moana Surfrider and The Royal Hawaiian. The Moana is a personal favorite for drinks and pupus (appetizers) at sunset. The original building is a large, grand hotel, with a lovely lobby. Walking through the lobby and towards the water, your eyes will be greeted by the sight of a massive banyan tree. It’s older than the hotel, and various tables are circled around it. The Beach Bar serves umbrella drinks and other pupus. Once you’ve had a few drinks, wandering down the beach to Duke’s for dinner is a great way to end the night, or get it started depending on whom you’re with. (Yes, Duke’s as in the surfer Duke Kahanamoku.) 

For sunset, grab seats on any of the catamarans that launch from the beach. I’ve been on almost all of them, and they’re all tons of fun. Depending on the age demographic, you might end up with a boat full of funny, incredibly intoxicated young people. Otherwise, it’s a fun cruise that sails out a ways for sunset. Hey, messing with drunken people can be fun. Snag seats on the nets at the front of the boat for the most fun, and wettest part of the boat.

The majority of Honolulu hotels can be found in Waikiki. Living on island, we get special local rates, and have done many overnights downtown.


9. Want a bird eye’s view of the island?
Hop aboard the one of the many helicopters the hover over the island with Blue Hawaiian Helicopters. Friends and family love them. Tours usually take you through the lush valleys of Hawaii, over the skyscraping mountains, and over cascading waterfalls. They fly pretty much all over the island, giving you a new perspective on famous places like Pearl Harbor and Waikiki. It’s around 200 bucks a ticket and each tour is 45 minutes, departing from Honolulu. You can book your tickets on their website. Before departure, double-check that camera battery. You’re going to want to have a fully-charged battery for this one.

8. First Friday in China Town
Like many cities, Honolulu does a huge first Friday party. All the restaurants and art galleries have extended hours. It attracts quite the crowd. Mostly consisting of younger people, you’ll meet a diverse set of people. Highly recommend touring the Honolulu Art Academy that night. It’s like a party, in the gallery! Honolulu’s China Town is an interesting one, for we have such a strong Asian influence present. I love Indigos. Located on Nuuanu Avenue, it’s Eurasian-influenced cuisine, and is very tasty!

7. Scuba Diving and Snorkeling
You’re in the Pacific! Sounds like it’s time to do some diving. I just got my diving certification; it’s as though a door to another world has been opened for me. Whether you’re a pro diver, a beginner, or just a snorkeler, Hawaii’s reefs are sure to impress.

I got certified with Aaron’s Dive Shop in Kailua. The address is: 307 Hahani Street Kailua, HI 96734. They lead many dive expeditions, give classes for certification, and sell a plethora of diving/snorkeling gear. One of my personal favorite dive sites is over in Hawaii Kai, on the southern side of the island. There isn’t much reef, but it’s earned the name Turtle Canyon.

A Honu's perspective

A Honu's Perspective

Plunging into the water, you’ll instantly see a honu, or turtle. Trust me when I say it won’t be the last turtle you’ll see on the dive. They come in every size and shape, and seem to be everywhere! It’s a shallow dive, not exceeding 50 feet. There isn’t much of a reef, but randomly placed statues of Buddhas, monkeys with swords, and girls reading books litter the floor. Eels like to make home in the stone, and poke their heads out often. Colorful fish swim by, and the water is crystal clear.



If you’re not a diver, throw on that mask and snorkel for a day in the warm blue waters! Hanauma Bay, again in Hawaii Kai, is a great place for fish spotting. It’s like stepping into a living mosaic underwater. In under an hour, you can see over 100 species of fish, including the humuhumunukunukuapua'a, and maybe even a honu or two.

One of my favorite spots to snorkel is off of Lanikai Beach, on the windward side. To get to Lanikai, make your way to Kailua, and follow the road until it ends, basically. Lanikai is a one-way loop; follow the loop to the park, take a left, and park anywhere on the road. There’s a public beach access that’ll drop you off on the beautiful beach.

6. Dolphin Excursion!
Hawaii is a playground for marine life. Whales, dolphins, turtles, sharks, rays, and fish, oh my! Dolphins can be commonly found on the leeward side of the island. There are two things you should know about that side: 1) the leeward side of Oahu is a very locally populated area, and most are not on the richer side. They don’t like tourists, so be wary of your surroundings. They won’t kill you, but they may get in your face yelling things. 2) Waianae is a long way from anything and everything. It’s out in the boonies. To see dolphins, you have to get up at an ungodly hour to make the trek. Dolphin tours run from Waianae Boat Harbor. It’s 120 bucks for adults, and 85 for kids ages 4-12. There’s a 10% discount if you drive yourself out there, otherwise, they’ll do hotel pick ups.

If you’re like me, you won’t spent that money. Instead, drive a little past the harbor, and park at a beach. Have a couple of floating items to rest on: boogie boards, noodles, surfboards, etc., and masks and snorkels. From there, leave and lock everything you’re not going to take, and swim out about a quarter to a half a mile. The dolphins literally swim through your legs. They can get so close, and playful. Personally, I think I’ll be a dolphin in another life. Don’t forget a waterproof camera!

5. Try your hand at the local water sports
Hawaii lives in the water. I know I certainly do. Getting out on the water is an excellent way to spend a day. In Waikiki, you can feel what it’s like to surf a six-man outrigger canoe. Feeling a bit more adventurous? Head over to the windward side of Oahu to Kailua and get a lesson in kite surfing on the beach the sport was invented on! We of course cannot forget about surfing itself! I know for a fact in Waikiki you can rent surfboards hourly. Highly recommend starting with a guide if it’s you’re first time surfing, but other than that, just go!

Want something fast? Is a jet ski fast enough? In Hawaii Kai, at Koko Head Marina, a variety of water sports/games are available: banana boating, jet skiing, water skiing, tubing, and parasailing!

Early Paddling Lanikai

4. Whale watching on the way to Costco
I’m not lying when I say I see whales going to and from Costco. In the winter, Humpback whales migrate down from Alaska to the islands to have their calves and raise them. Dinner cruises out of Honolulu offer dance parties and whale watching all in one unforgettable evening. Being even marginally close to a whale is magical, something you’ll never forget. The best times to spot whales are around January to late March. By April, they’ve all started back towards Alaska. Expect dinner cruises with whale watching to be somewhere around $100-$200 per head. If you want to save a few bucks, driving along the south shore of Oahu along Kalanianaole Highway is the best viewing site. There are many pull offs for pictures, and is just a beautiful drive in general. Good luck, whale spotters!

3. Hiking!
You an outdoorsy type? I’ve got to say, you’ve come to the right place. Oahu has a diverse set of trails, from the family friendly to the extreme. One of my absolute favorite hikes to do is the simple pillbox hike. The hike is just under two miles round trip. The first part is steep, and at times, slippery. After that, the hike’s easy and family-friendly. The views are gorgeous, giving breath taking vistas of Lanikai and the Mokulau Islands, Kailua Bay, surrounding mountains, and even far of Kaneohe. To get there, drive into Kailua, and get on Kalaheo Ave. Follow it into Lanikai, and take a right onto Kaelepulu Drive. Park wherever, and take a left on the street before the country club gates. The trailhead is at the top of the road on the right.

Looking for extreme? Brave the Pali Puka to Lanihuli ridge hike. Trek along the tower Koolau ridge. With only a few feet in width, and 2000 plus foot vertical drop on both sides, it’s not one for the faint hearted. The trailhead can be found at the Pali Lookout off of the Pali Highway.

There are no shortages of trails on island. The infamous Stairway to Heaven can be scaled, as well as many other family hikes.

Sunrise from the Pillboxes

sunrise from the pillboxes

2. Want to see classic Hawaii? Head toward the North Shore!
Whenever I mention Haleiwa to mainlanders, they get a dreamy look in their eyes, trying to imagine what the iconic surf town might be like. It’s definitely what most people might expect of Hawaii. This sleepy, little beach town is tiny. It only takes 15 minutes to wander up the town’s main drag.

My favorite way to spend time on the North Shore starts off early. I mean really early with a shark cage snorkel. From Kailua to Haleiwa is every bit of an hour, plus some. The best time to see the most sharks is early, the first tour departing Haleiwa at 7am. I like to go with North Shore Shark Adventures. Why? They’re environmentally friendly, and have other incentives other than to make money. The best time to do the tours is in the summer; winter in Hawaii means big surf for the island, as in 50 plus foot waves. It’s when we do the huge surf competitions, which are tons of fun to see. Don’t do the shark cage in the winter though because a) people prone to seasickness are going to die and b) the conditions are not as clear.

Once your life-changing shark snorkel is finished, head down to Haleiwa Café on Kamehameha Highway. The home fries and pancakes are my favorite thing to order. After a quick and onolicious breakfast, hit the road again and follow Kamehameha Highway as it weaves it’s way down the coast. The first stop you’ll want to hit is what we call Turtle Beach. The beach is really called Laniakea Beach; there are no real landmarks coming from Haleiwa. It should be the second or third beach you pass by. On the makua side, there will be a large group of cars parked. Park, and cross the street to the beach. Walk to the far end of the beach, the south side - that’s where the turtles like to hangout. Remember it is illegal to touch the turtles, for they are endangered. They have personal bubbles too.

Following the road, you’ll come across many famous beaches like Pipeline, Sunset, and Waimea. If it’s winter, do not enter the water. The rip currents will take swimmers out to sea, and the waves are massive. Swim at these places only in the summer. Then, the water is flat, crystal clear, and there’s a chance of spotting a pod of dolphins.

1. Kailua!
Kailua is Oahu’s new best-kept secret, and just happens to be my hometown. Located on the windward side of the island, it’s only about 30 minutes from the bustling world of Honolulu, yet it seems a world away.

Street fair, downtown Kailua

Street fair, downtown Kailua

Kailua Beach, and its neighbor Lanikai Beach, have been nominated as the most beautiful beaches in the world numerous times by many travel websites and magazines. Nestled between the towering green Koolaus and sparkling, warm, aqua ocean, Kailua is just beginning to be discovered by mainlanders.

Lanikai Beach

Lanikai Beach

Many cute, independent shops and restaurants dot the town. A few of my favorites, and not to be missed stops, include Kalapawai Deli, Lanikai Juice, Bob’s Pizza, Baci Bistrio, and Yogurt Mama. Seriously, not visiting these places would be like committing a crime. Wandering Kailua’s people friendly streets, you’re bound to find shops you like and food you’ll love. Oh, if you want to the best breakfast you’ll ever have, head over to Mokes. They legitimately have the best pancakes in the world, no jokes.

 Acai Bowl - double YUMmy!

Acai Bowl - double YUMmy!

Lanikai Juice... YUM

Lanikai Juice... YUM

Kailua is pretty small, so everything is walkable. From Kailua, it’s about a 15 or 20 minute walk to the beach. One of my favorite things to do while home is kayaking out to the Mokes. The Mokulua Islands are two islands about a mile of shore.

the Mokes

the Mokes

There are many tours that run trips out to the islands daily. I recommend these tours, for a massive reef acts like a barrier between the islands and beach. If you don’t know how to navigate it, you may end up in a pretty sticky situation. Prices for a tour can range anywhere from a $100-$125, and that includes lunch, hotel pickup, and snorkeling, plus the expedition.

Rainbow over Haleiwa

I’ve circled the globe, and seen and done some pretty amazing things. But there’s something special about Kailua that makes it the best place in the world.

To find the best place to stay, search for vacation rentals in Oahu with cozycozy.


Austin Weihmiller is a member of the Youth Travel Blogging Mentorship Program


All photos courtesy and copyright Austin Weihmiller